


The Deal

by SinQueen69



Series: Requests [24]
Category: Teen Wolf (TV)
Genre: Age Difference, Always Female Stiles Stilinski, Anal Fisting, Anal Sex, Chastity Device, Clit Play, Creampie, Dirty Talk, Don't copy to another site, F/M, Female Stiles Stilinski, Genderbend, Humiliation kink, Loss of Virginity, Older Man/Younger Woman, Prompt Fill, Pussy Spanking, Rough Sex, Squirting, Underage - Freeform, Vaginal Fingering, Vaginal Sex, Verbal Humiliation
Language: English
Status: Completed
Published: 2020-04-13
Updated: 2020-08-05
Packaged: 2021-03-01 22:20:17
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 2
Words: 2,429
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23634481
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Anon on Tumblr wanted: Would you please write female stiles? Derek fucking girl Stiles in the ass while slapping her pussy and rubbing her clit to making her squirt. Stiles Stilinski/Derek Hale, anal sex, pussy slapping, squirting. Thank youRequest Anon wanted a sequel
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [24]
Series URL: https://archiveofourown.org/series/1618726
Comments: 9
Kudos: 781





	1. Chapter 1

“Come on Der, please?” Stiles wiggled her hips against Derek, fluttering her eyelashes at him before pouting when Derek sent the teen an unimpressed look. 

“You know the deal Stiles,” Derek said as he tapped the fat head of his cock against the teen’s asshole. 

“I hate that deal,” Stiles pouted as she adjusted her hold on her legs, keeping them open and wide around the older man’s body. 

“You agreed to it until you graduate high school you are nothing but my little anal slut,” Derek smirked as he pushed his cock into her ass. Stiles gasped at the words and the familiar stretch in her ass as Derek’s cock entered her. 

“F-Fuck!” Stiles panted as she did her best to keep her trembling legs open as Derek’s balls settled against her in the way they usually did when he was fully seated inside of her ass. 

“I love how wet your cunt gets when I fuck your ass,” Derek mused as he used his thumbs to spread her pussy lips apart, licking his lips at the sight of the glistening pink folds. Derek’s cock twitched inside of Stiles’ tight ass at the thought of pounding into that wet cunt. Derek just had to be patient and then he would be able to fuck all of Stiles’ holes whenever he wanted. 

“Derek,” Stiles whined, cheeks pink as she watched him spread her empty pussy open and stare at it with dark eyes. 

“Not yet, but soon,” Derek promised aloud before he released his hold on her pussy before pressing his thumb against her clit. Stiles mewled and squirmed as he applied harsh pressure to it, her ass flexing around Derek’s length. 

Stiles let out a cry when Derek removed his thumb and suddenly spanked her cunt, sending sparks of pain laced pleasure through her body. Her nipples peaked and her hands lost their grip on her legs, allowing them to fall onto the bed on either side of the older man. 

“Remember your place, what does my anal slut do when I’m in her ass again?” Derek questioned, watching as Stiles’ face went red to match her pussy. Stiles planted her feet on the bed and started to move her hips while she cupped her breasts and began to roll and pinch her stiff nipples, little gasps falling from her lips as she did so. 

“Mm, that’s right, fuck yourself on my cock.” Derek grinned sharply as he stayed still to watch as her asshole stretched and contracted around his cock as the teen did her best to fuck herself on his shaft. 

“Just remember that when you graduate high school, you also graduate from just being my anal slut to my full-service slut.” Derek reminded as he brought his hand down on her cunt again, unable to help himself and enjoyed the way she got wetter each time he spanked her pussy and the cute cry she would always let out. 

“I, oh fuck, I want that Derek.” Stiles panted out, she had agreed to this. She had agreed to be his anal slut, so desperate to be fucked by the older man she had eagerly offered up her ass to him and she never regretted it. As it turned out she loved anal and Derek’s rough, humiliating behaviour in bed as she thought she would. 

“Of course you do, you’re a natural born slut.” Derek hummed as he pinched and teased her engorged clit as she worked her ass over his cock repeatedly. Stiles moaned at the new slightly painful simulation before shuddering when Derek’s next hit landed on her clit. A familiar pressure was building up in her stomach and she squeezed her breasts harder and clenched around the older man’s cock tighter. 

“Derek, fuck, I think I’m close!” Stiles panted out, back arching when Derek suddenly slammed into her ass roughly. 

“Oh, are you? Is my little anal slut going to squirt? Such a little whore, coming just from my cock in your ass and my hand spanking your soaked cunt.” Derek crooned out the humiliating words as he landed a few more hard spanks on her aching pussy and harshly pinched her clit for good measure.

Stiles cried out as she all but lurched up from the bed as the pressure she had felt exploded out of her while her body clamped down on Derek’s thick cock while her empty cunt convulsed and her release squirted out of her. 

“Such a messy little anal slut you are,” Derek commented, breathless from watching the teen squirt below him. It was a sight he would never tire of and he gripped her hips, lifting her so he could properly fuck her ass. Stiles mewled and writhed as she clung to the bedsheets below her as she took each almost brutal thrust from the older man.

“Fuck!” Derek groaned out as he tossed his head back as he came deep in the teen’s ass as he had many times before. He slipped his softening cock out of her now gaping and cum-dripping hole and lowered the exhausted teen back onto the bed. 

“Just think, only a few more months and then you get to feel my hot cum in your cunt. Won’t that be a nice graduation present my little anal slut?” Derek brushed her hair off of her face as his free hand cupped her throbbing and heated cunt, resisting the urge to dip his fingers into her virgin slit. 

“So good Derek, I can’t wait.” Stiles beamed if his cock and cum felt that good in her ass, she couldn’t wait to feel it in her pussy. She tugged her older boyfriend down for a sloppy kiss as she felt his cum ooze out of her clenching ass in a lewd way that she had come to love.


	2. Chapter 2

**Summary for the Chapter:**

> Request Anon: Could you do a second part of "The Deal" where it's female Stiles' birthday and Derek and Stiles finally have vaginal sex? Stiles Stilinski/Derek Hale, vaginal sex, squirting, pussy slapping, fisting (it can be ether vaginal or anal). Thank You so much

**Notes for the Chapter:**

> Tags: Anal sex, anal fisting, pussy spanking, squirting, butt plug, creampie, vaginal sex, dirty talk, loss of virginity, vaginal fingering, spreader bar, rough sex, chastity belt, slight Somnophilia

“Be quiet, unless you want someone to walk in on you like this. Bent over and begging an older man to come in your ass.” Derek sounded amused from where he was pressed against Stiles’ back. Stiles was bent over a desk in an empty classroom, the whole school outside, waiting for graduation to start. Yet Stiles was here with her graduation robe hitched up around her stomach and Derek plowing her ass and hands groping her breasts roughly. 

“Then come in me before someone comes looking,” Stiles shot back before covering her mouth with her hand when Derek spanked her pussy just as he drove his cock deep into her ass, filling her with his hot come a moment later. 

Stiles inhaled sharply when he pulled out of her ass before shoving a plug into her ass to keep his come inside of her. Derek pulled her upright, smoothing her graduation robe back into place with a smug look on his face when he saw her flushed cheeks and dilated eyes.

“You’re going to graduate with my come in your cute little ass and then once your party is finished you’re going to come home with me and I’ll fill your needy little cunt like the way you’ve been begging me to do for so long,” Derek promised darkly, his hand sneaking under the robe once more to spank her wet cunt, earning a keen from the teen who quickly bit her lower lip to focus herself. 

“Okay, see you after I graduate.” Stiles went up on her tiptoes to kiss Derek before she limped out of the classroom, her nipples sore, her cunt aching and ass plugged. This was going to be a long night. 

~~//~~

Stiles was right, by the time Graduation plus the party was finished. She was exhausted but filled with excitement for what was going to come next as she and Derek stumbled into his bedroom, clothes flying every which way and Stiles was horny all over again. The plug had been a good grounding point throughout the day, even if she had to blush and wiggle a bit more than she would have liked to get comfortable in her chair during the speeches. 

“Finally, my little anal slut is going to become a proper slut.” Derek crooned as he pinched her nipples as she humped against his thigh desperately.

“I’ve been waiting for so long,” Stiles panted as her cunt throbbed in arousal as Derek wiggled the plug in her ass. 

“You have one more step before you get my cock in your greedy cunt.” Derek reminded and Stiles clenched around the plug as her cheeks burned as she remembered the last bit of the deal they had made when she first agreed to this. 

“Lay down,” Derek ordered and Stiles dramatically threw herself face down onto the bed, wiggling impatiently even as Derek locked her wrists and ankles into spreader bars before forcing her up onto her knees in the classic face down, ass up position. 

Stiles shuddered as the lug was pulled out of her ass, allowing some of Derek’s come to drip out of her as the sound of lube being opened echoed out. 

The first three fingers went into her ass with ease, she was used to that considering the size of Derek’s cock that she took on a near-daily basic. The addition of Derek’s pinky added a bit of a burn but nothing Stiles couldn’t handle as she rocked back against Derek’s four fingers, the copious amounts of lube and Derek’s previous load of cum easing the slide. 

“Ready?” Derek asked, breathless with arousal and excitement as he tucked his thumb against his palm.

“Hell yes,” Stiles relaxed as she felt Derek start to push his hand forward. She squeezed her eyes closed as her hole opened wider and wider to accept the width of the older man’s hand. Stiles was glad for the bars, they kept her in place instead of wiggling all over the place which would have made taking Derek’s fist harder. 

Derek wet his lips as he watched as his fist popped into the teen girl’s ass, her rim clinging desperately to his wrist as he slowly made a fist inside of her tight ass. Stiles moaned and arched back against him when he began to slowly, gingerly fuck her ass with his fist. He didn’t want to completely ruin her ass as he stilled planned on fucking it in the future so he just kept the slow, gentle pace while he enjoyed the lewd sight of his fist deep inside of her ass. 

Derek could have done this all night, but he did promise Stiles he would fuck her cunt and to be honest he had been aching to bury himself in that tempting hole of her’s since they first met. 

Derek slowly unfurled his fist and eased his hand out of her now gaping hole and he watched it clench and flex uselessly for a moment before he cupped her wet cunt for a moment before he slapped it harshly. Stiles squealed at the sudden movement, body jerking as she squirted out her orgasm, obviously having been on the edge when Derek had fisted her. 

“Such a fucking slut, squirting from me fisting your ass like that.” Derek laughed as he spanked her pussy over and over, watching her squirm below him and gaping hole twitch and flex desperately. Derek shoved two fingers into her cunt and roughly fingered her until she was crying out again, gushing over his hand as she sobbed out her second orgasm. 

“Remember, once an anal slut always an anal slut.” Derek reminded even as he lubed up his cock, placing it at her slick folds, finally ready to push into her virgin cunt. 

“Ah! Fuckkkk Derek!” Stiles wailed out as Derek slid his large cock into her soaked, sensitive pussy. Derek went in with ease and he wasted no time in fucking her like he fucks her ass, from the way her hot, tight cunt was squeezing his cock like a vice grip and she was fucking back against him, Derek knew Stiles loved it. 

Derek spanked her full cunt over and over as he fucked it raw, Stiles was moaning and sobbing now as she was forced through another orgasm by his sadistic actions. 

Stiles was shaking and whimpering by the time her third orgasm calmed down and she felt so beyond wrung out, she couldn’t tell up from down as Derek fucked her over sensitive cunt while slapping her clit repeatedly. 

“Remember slut, you wanted this. You wanted to be a proper slut and not just my little anal slut. You asked for this.” Derek reminded, voice dark and low in her ear and Stiles sobbed as she felt his burning hot cum flood into her aching and sore cunt. 

“Remember your manners slut,” Derek slapped her cunt again as he pulled out, leaving her wet and messy and leaking his cum from both holes. 

“T-Thank you for making me your slut Derek.” Stiles whimpered out before she collapsed fully, passing out completely. 

~~//~~

Derek petted Stiles’ hair the next morning, lazily thrusting in and out of her still wide open ass, using her hole as a place to relieve his morning erection. 

Stiles’ nose wrinkled up as she slowly woke up, smacking her lips together before she peered over her shoulder to look at her lover.

“M-Morning,” Stiles moaned when she realized that he was fucking her ass already. Stiles shifted before stilling and her hand flew down to her crotch, making a confused noise when her hand touched metal. She quickly looked down and choked a bit at the sight of a metal chastity belt locked around her groin. 

“I thought about it after you passed out last night, it seems you being my proper slut may be too much for you to handle right now. So until I think you can handle it, you’re going to stay my little anal slut. This is for your own benefit Stiles, I’m doing this for you.” Derek crooned as he cupped her breasts as he spoke and rutted into her ass.

“Y-Yeah, it was intense last night.” Stiles swallowed as her sore cunt ached from underneath her new chastity belt. 

“So anal only for now Stiles, just until you can handle taking my cock in your cunt again,” Derek promised, hiding his smirk as she nodded slowly. 

“Just for a little while,” She agreed to his new deal as she caressed her new belt for a moment before shuddering when she felt Derek’s cum flood her ass, things were the way they should be. She was his little anal slut after all.


End file.
